CA2953798A1 - Composes aminopyridazinone a utiliser en tant qu'inhibiteurs de proteines kinases - Google Patents

Composes aminopyridazinone a utiliser en tant qu'inhibiteurs de proteines kinases Download PDF

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Publication number: CA2953798A1
Authority: CA; Canada
Prior art keywords: unsubstituted; substituted; group; compound; pharmaceutically acceptable
Prior art date: 2014-07-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA2953798A

Other languages

English (en)

Other versions

CA2953798C (fr

Inventor

Dong Liu

Minsheng Zhang

Qiyue Hu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Jiangsu Hengrui Medicine Co Ltd

Original Assignee

Eternity Bioscience Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2014-07-07

Filing date

2014-10-20

Publication date

2016-01-14

2014-10-20 Application filed by Eternity Bioscience Inc filed Critical Eternity Bioscience Inc

2016-01-14 Publication of CA2953798A1 publication Critical patent/CA2953798A1/fr

2019-06-11 Application granted granted Critical

2019-06-11 Publication of CA2953798C publication Critical patent/CA2953798C/fr

Status Active legal-status Critical Current

2034-10-20 Anticipated expiration legal-status Critical

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VROMXVIODDASTK-UHFFFAOYSA-N 5-amino-1h-pyridazin-6-one Chemical class NC1=CC=NNC1=O VROMXVIODDASTK-UHFFFAOYSA-N 0.000 title description 2
229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
239000003909 protein kinase inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 153
206010028980 Neoplasm Diseases 0.000 claims abstract description 19
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 58
150000003839 salts Chemical class 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 40
239000012453 solvate Substances 0.000 claims description 40
239000000651 prodrug Substances 0.000 claims description 38
229940002612 prodrug Drugs 0.000 claims description 38
239000002207 metabolite Substances 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical group 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 28
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 19
125000005415 substituted alkoxy group Chemical group 0.000 claims description 18
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
125000003107 substituted aryl group Chemical group 0.000 claims description 17
-1 nitro, hydroxyl Chemical group 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 12
210000004027 cell Anatomy 0.000 claims description 11
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
210000003719 b-lymphocyte Anatomy 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 7
125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
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208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 6
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229910052799 carbon Inorganic materials 0.000 claims description 6
206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 claims description 5
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208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 3
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125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
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238000002953 preparative HPLC Methods 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
239000007832 Na2SO4 Substances 0.000 description 8
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125000000217 alkyl group Chemical group 0.000 description 8
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
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238000003419 tautomerization reaction Methods 0.000 description 1
CMIBWIAICVBURI-SSDOTTSWSA-N tert-butyl (3r)-3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](N)C1 CMIBWIAICVBURI-SSDOTTSWSA-N 0.000 description 1
UIJXHKXIOCDSEB-QMMMGPOBSA-N tert-butyl (3s)-3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H](O)C1 UIJXHKXIOCDSEB-QMMMGPOBSA-N 0.000 description 1
STYSIWNZDIJKGC-YUMQZZPRSA-N tert-butyl (3s,4s)-3-amino-4-methoxypyrrolidine-1-carboxylate Chemical compound CO[C@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1N STYSIWNZDIJKGC-YUMQZZPRSA-N 0.000 description 1
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125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Epidemiology (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Oncology (AREA)
Hematology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA2953798A 2014-07-07 2014-10-20 Composes aminopyridazinone a utiliser en tant qu'inhibiteurs de proteines kinases Active CA2953798C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201462021421P	2014-07-07	2014-07-07
US62/021,421		2014-07-07
PCT/US2014/061393 WO2016007185A1 (fr)	2014-07-07	2014-10-20	Composés aminopyridazinone à utiliser en tant qu'inhibiteurs de protéines kinases

Publications (2)

Publication Number	Publication Date
CA2953798A1 true CA2953798A1 (fr)	2016-01-14
CA2953798C CA2953798C (fr)	2019-06-11

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ID=55064639

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CA2953798A Active CA2953798C (fr)	2014-07-07	2014-10-20	Composes aminopyridazinone a utiliser en tant qu'inhibiteurs de proteines kinases

Country Status (15)

Country	Link
US (2)	US9951077B2 (fr)
EP (1)	EP3166608B1 (fr)
JP (1)	JP6409116B2 (fr)
KR (1)	KR102073797B1 (fr)
CN (2)	CN106573001B (fr)
AU (1)	AU2014400628B2 (fr)
BR (1)	BR112017000470B1 (fr)
CA (1)	CA2953798C (fr)
ES (1)	ES2706745T3 (fr)
MX (1)	MX2017000331A (fr)
PL (1)	PL3166608T3 (fr)
RU (1)	RU2674701C2 (fr)
TW (1)	TWI711619B (fr)
WO (1)	WO2016007185A1 (fr)
ZA (1)	ZA201700115B (fr)

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JP6966044B2 (ja) *	2016-06-22	2021-11-10	シャンハイフォチョンファーマシューティカルカンパニーリミテッド	タンパク質キナーゼ阻害剤としての置換されているピロロ［２，３−ｄ］ピリダジン−４−オン及びピラゾロ［３，４−ｄ］ピリダジン−４−オン
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JP2021521208A (ja)	2018-04-13	2021-08-26	江蘇恒瑞医薬股▲ふん▼有限公司	ピロロアミノピリダジノン化合物およびその中間体の製造方法
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CN111499642A (zh) *	2019-01-31	2020-08-07	江苏恒瑞医药股份有限公司	吡咯并[2,3-d]哒嗪-7-酮类衍生物的可药用盐、晶型及其制备方法
CN113825511B (zh) *	2019-05-31	2024-10-22	江苏恒瑞医药股份有限公司	一种固体分散体及其制备方法
CN110372562B (zh) *	2019-07-09	2021-04-06	上海再启生物技术有限公司	一种btk激酶抑制剂关键中间体的晶型及其制备方法
WO2021057998A1 (fr) *	2019-09-29	2021-04-01	上海森辉医药有限公司	Procédé de préparation d'un composé de pyrroloaminopyridazinone
CN112745255A (zh) *	2019-10-30	2021-05-04	江苏恒瑞医药股份有限公司	一种btk激酶抑制剂的制备方法
US20230270743A1 (en) *	2020-08-10	2023-08-31	Jiangsu Hengrui Pharmaceuticals Co., Ltd.	Use of btk inhibitors in the treatment of diseases
WO2022042612A1 (fr) *	2020-08-27	2022-03-03	上海和誉生物医药科技有限公司	Dérivé de dihydropyrrolo[2,3-d]pyridazin-7-one, son procédé de préparation et son utilisation
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WO2022242752A1 (fr) *	2021-05-21	2022-11-24	江苏恒瑞医药股份有限公司	Procédé de préparation d'un intermédiaire d'inhibiteur de btk
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CN118139626A (zh) *	2021-09-01	2024-06-04	江苏恒瑞医药股份有限公司	一种pi3k抑制剂与btk抑制剂在制备治疗淋巴瘤的药物中的用途
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2014
- 2014-10-20 CA CA2953798A patent/CA2953798C/fr active Active
- 2014-10-20 KR KR1020177002250A patent/KR102073797B1/ko active Active
- 2014-10-20 AU AU2014400628A patent/AU2014400628B2/en active Active
- 2014-10-20 CN CN201480080486.2A patent/CN106573001B/zh active Active
- 2014-10-20 JP JP2017500344A patent/JP6409116B2/ja active Active
- 2014-10-20 CN CN201811358086.XA patent/CN109970741B/zh active Active
- 2014-10-20 RU RU2017103757A patent/RU2674701C2/ru active
- 2014-10-20 BR BR112017000470-4A patent/BR112017000470B1/pt active IP Right Grant
- 2014-10-20 WO PCT/US2014/061393 patent/WO2016007185A1/fr not_active Ceased
- 2014-10-20 MX MX2017000331A patent/MX2017000331A/es active IP Right Grant
- 2014-10-20 US US15/323,929 patent/US9951077B2/en active Active
- 2014-10-20 ES ES14896967T patent/ES2706745T3/es active Active
- 2014-10-20 PL PL14896967T patent/PL3166608T3/pl unknown
- 2014-10-20 EP EP14896967.8A patent/EP3166608B1/fr active Active
2015
- 2015-06-03 TW TW104117984A patent/TWI711619B/zh not_active IP Right Cessation
2017
- 2017-01-05 ZA ZA2017/00115A patent/ZA201700115B/en unknown
2018
- 2018-02-27 US US15/906,934 patent/US10323037B2/en active Active

Also Published As

Publication number	Publication date
CN109970741A (zh)	2019-07-05
CN106573001B (zh)	2019-01-29
JP2017522302A (ja)	2017-08-10
ES2706745T3 (es)	2019-04-01
EP3166608A4 (fr)	2017-11-22
US9951077B2 (en)	2018-04-24
RU2674701C2 (ru)	2018-12-12
US20180251465A1 (en)	2018-09-06
WO2016007185A1 (fr)	2016-01-14
MX2017000331A (es)	2017-08-25
TWI711619B (zh)	2020-12-01
KR102073797B1 (ko)	2020-02-05
ZA201700115B (en)	2020-05-27
TW201625626A (zh)	2016-07-16
EP3166608A1 (fr)	2017-05-17
CA2953798C (fr)	2019-06-11
BR112017000470B1 (pt)	2022-11-29
RU2017103757A (ru)	2018-08-07
AU2014400628A1 (en)	2017-01-19
CN106573001A (zh)	2017-04-19
KR20170023156A (ko)	2017-03-02
US20170152264A1 (en)	2017-06-01
CN109970741B (zh)	2020-07-28
JP6409116B2 (ja)	2018-10-17
PL3166608T3 (pl)	2019-07-31
BR112017000470A2 (pt)	2017-11-07
RU2017103757A3 (fr)	2018-08-07
US10323037B2 (en)	2019-06-18
EP3166608B1 (fr)	2018-12-12
AU2014400628B2 (en)	2019-05-02

Publication	Publication Date	Title
CA2953798C (fr)	2019-06-11	Composes aminopyridazinone a utiliser en tant qu'inhibiteurs de proteines kinases
RU2759678C2 (ru)	2021-11-16	Соединения и композиции в качестве ингибиторов эндосомальных toll-подобных рецепторов
ES2865199T3 (es)	2021-10-15	Compuestos de heteroarilo o arilo condensados bicíclicos como moduladores de IRAK4
KR101864561B1 (ko)	2018-06-04	Jak 억제제
CN103889962B (zh)	2017-05-03	作为受体酪氨酸激酶btk抑制剂的取代的n‑(3‑(嘧啶‑4‑基)苯基)丙烯酰胺类似物
EP3080121B1 (fr)	2019-09-04	Dérivés de benzoimidazoles fusionnes tricycliques utilisables en tant que modulateurs de l'activité tnf
KR20160144378A (ko)	2016-12-16	브루톤 티로신 키나제 억제제로서 작용하는 폴리플루오로화 화합물
AU2014323777A1 (en)	2016-04-28	Compound inhibiting activities of BTK and/or JAK3 kinases
CA2933480A1 (fr)	2015-06-18	Inhibiteur de la demethylase-1 specifique de la lysine
BR112019023918A2 (pt)	2020-06-02	Inibidores de quinase e usos dos mesmos
KR20230016219A (ko)	2023-02-01	Il-17a 조절제
KR20250121029A (ko)	2025-08-11	두드러기 치료를 위한 야생형 c-kit 키나제 억제제로서의 n-페닐-피라졸로[1,5-a]피리딘-3-카르복사미드 유도체
WO2016192630A1 (fr)	2016-12-08	Composé présentant une activité inhibitrice de kinase, son procédé de préparation, et utilisation de celui-ci
WO2011152485A1 (fr)	2011-12-08	Nouveau dérivé de pyrimidine condensé en 4,5
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